Described as: "Beautiful, young, vocally gifted, a choir singer with an obviously sparkling career stretching before her. She staggared everyone who knew her by first appearing in his cabaret and then marrying Giacomo "Big Jim" Colosimo." Colosimo was a mob boss.

Born in Ohio to a Mr. Frank Winter and Estelle H. Ziegler Winter. Lived in Columbus Ohio. She had a brother named Clyde.

Dale Winter was first married to Chicago Underworld figure Giacomo "Big Jim" Colosimo. She was married to Colosimo only one week before he was assassinated on May 11, 1920 in his own restaurant. Allegedly, she signed over all rights to his estate including jewelry etc. after his death. Colosimo's first wife, Victoria Moresco had been a madam and they owned several brothels as well as being involved in all other aspects of crime. As a young woman, Dale Winter toured the Orient with her mother and, upon returning to Chicago worked in Giacomo's nightclub. After Giacomo Colosimo's death, Dale married theatrical producer, Henry Duffy, who was divorced from Anne Nichols, author of "Abie's Irish Rose." In the 1930s Dale and her new husband lived on Brewer Avenue in San Mateo California in a house worth $75,000. Her mother, Estelle Winter lived with the couple as well as a cook and a butler. It appears that Dale later married a Mr. Perot because she is listed under that name at the time of her death on November 28, 1985 in Santa Barbara California.she had two children, 4 grandchildren and three great grandchildren. She was 95 years old when she died from heart failure.

Formed Dufwin Theatres with second, husband Henry Duffy. She adopted two children with Duffy: Patricia Dale ( was Patricia Harris and adopted from a family friend) and David. She divorced Duffy in 1950. Married twice after Duffy. She married an Edward S. Perot, an industrialist and he died in 1963.